This volume features the following stories depicting the corporal punishment of teenage boys:

Caught Spying on the Slumber Party: Bobby is caught spying on his stepsister and five of her hot friends on a sleepover. Furious, his dad humiliates him by inviting each of the girls to whip Bobby with his belt, with his stepmother delivering the final blows.

The Spanking Glove: Bobby has pushed his sister over in the back garden and his mother spanks him with her gloved hand. Realising how effective the glove is, his mother purchases another pair to be used solely for spanking.

Needing a Math Tutor: Brian's grades have slipped due to lack of effort. His mom delivers some 'encouragement' but decides a tutor is needed. Rachel has a unique method of motivation and applies it liberally, showing herself to be a consummate professional with the paddle.

Tracking in Trouble: A teenage boy with a penchant for car repair keeps tracking grease and dirt into his mother's clean house. Since he cannot keep from marking up the house she decides to mark up his bottom!

A Mother is Disgraced by an Undisciplined Child: David has an extremely religious and super strict mother, who has raised him with weekly Sunday paddlings. When he goes away to college he thinks he's free now to do as he pleases. To his surprise his mom is wise to his transgressions and upon returning home on break he is shown that she's still very much in charge.

Providing an Outlet for Mom: Michael works out that acting like his absent, obnoxious dad provides an outlet for his mom to whip his butt and therefore relieve the tension. He is willing to take the pain to help her.

Payback for Spying: A geeky high school boy with no prospects of finding a real girlfriend contrives a plan to set up a hidden camera in the girls' locker room. He makes the mistake of bragging about it a bit too loud and is found out by the boyfriend of one of the girls who sets in motion a plan to make sure the evidence never comes to light.

I'm My Own Worst Enemy: Michael is supposed to go straight home from school as he's grounded. But he disobeys his mom and stops at a friend's house. However, his mom catches him out and orders him to fetch the hairbrush.

Rolling for Damage: Charlie is horrified to learn that his mom is going to use his gaming strategy by rolling his dice to determine not only which implement is used to punish him, but the number of strokes he will receive.